Synthesis of EnantiopureN-tert-Butoxycarbonyl-2-aminocycloalkanones
- 1 November 1992
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 22 (20) , 3003-3012
- https://doi.org/10.1080/00397919208021127
Abstract
A route to enantiomerically pure N-tert-butoxycarbonyl-2-aminocycloalkanones (ring size: 5-8 membered) from the corresponding cycloalkene oxides is described. The procedure involves (1) aminolysis with (S)-α-methylbenzylamine/Me3A1 and chromatographic separation of diastereomers, (2) hydrogenolysis to afford the trans-2-aminocycloalkanols, (3) tert-butoxycarbonyl (Boc) protection, and (4) PCC oxidation.Keywords
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